Angela Palumbo
Apple has reached a turning point. When CEO Tim Cook delivers the keynote address at the company's Worldwide Developers Conference on Monday, it will likely be his last major public act as chief executive. He would sure like to go out with a bang.
The company has an agenda to meet the moment. WWDC is shaping up to be Apple's second attempt at announcing its plans for artificial intelligence. The company first rolled out Apple Intelligence at 2024's WWDC.
Wall Street expected that 2024 rollout to drive a massive iPhone upgrade cycle. Instead, Apple's AI products have disappointed consumers, and the launch of a highly anticipated AI-powered Siri chatbot has been delayed until the fall.
Now, it's take two. Apple is expected to show off a revamped Siri during the keynote on Monday, along with some other AI updates. UBS analyst David Vogt expects Apple to present an AI-powered Siri that will be able to understand personal data and analyze on-screen content. He also expects Apple to launch an independent Siri app that functions similarly to other AI apps by acting as an "interface for text, voice, and attachments."
After getting punished on its AI failures, Apple stock is rallying again. Investors are offering Apple a rare second chance to get AI right.
"I think this would be a great opportunity to just show that personalized Siri is the killer consumer agent," John Belton, portfolio manager at Gabelli Funds, tells me. "Maybe personalized Siri is something that can really bring a lot of this new technology to the billions of iPhone users around the world."
This WWDC holds emotional weight for the company and its fans. Cook is stepping down from his role in September, and incoming CEO John Ternus is expected to lead the announcement of the next iPhone that month.
By any financial metric, Cook's tenure has a been a wild success. Revenue is up 293%. Market value has increased $4.2 trillion. Cook, meanwhile, has turned Apple into a services business with a sticky ecosystem. He spearheaded the launch of wearable products like the Apple Watch and AirPods. Monday's WWDC keynote gives Cook an opportunity to leave the company on an even more positive note.
"The most important message they're gonna have to tell is, 'We're not behind in AI. We have a game plan. We have a strategy.' And I think if that vision is shared by Tim Cook, then he'll be leaving at a time when he has sort of set the company up for the next era. And from that standpoint, I think it's a pretty logical time to be transitioning out," Belton says.
Any progress in AI comes amid a difficult backdrop. Public sentiment around AI has quickly shifted, with worries about job loss and privacy overshadowing any productivity enhancements the technology might bring. Half of U.S. adults say the increased use of AI in daily life makes them feel more concerned than excited, according to a 2025 survey from Pew Research Center.
The negativity could actually be a boon for Apple, which has long marketed itself as a company that prioritizes user privacy and safety. Users already share huge amounts of data with Apple, from passwords and credit cards to Face IDs and their most personal health information.
Apple has another edge in the AI race. It isn't spending hundreds of billions of dollars on capital expenditures. While Alphabet parent is suspending stock buybacks and turning to equity markets to raise more money, Apple continues to repurchase shares. If Apple gets AI right, its spending strategy will look brilliant.
For now, Apple seems to be following its successful old playbook. The company never created its own search engine, relying on Google to power search across its devices. Apple is religious about controlling customer experiences, but it knows where to ask for help.
When it comes to AI, Apple has announced previous plans to partner with ChatGPT maker OpenAI on Apple Intelligence. This year, the company said its next generation of Apple Foundation Models would be based on Google's Gemini models and cloud technology.
"Apple has not been a visible participant in the compute buildout race, and frontier model-building is not where the company has historically differentiated vs. other Mag Seven peers or frontier labs. This has fed the perception that Apple is an AI laggard in a race that is already well underway," BofA Securities analyst Wamsi Mohan recently wrote in a note to clients.
But, Mohan said, Apple doesn't have to own the best frontier model if it owns the "trusted interface."
Investors seem to understand that Apple is playing a wise long game when it comes to AI. Over the past 12 months, Apple shares have jumped 54%, doubling the S&P 500's gain.
For Cook & Co., the rally has raised the stakes for Monday's event. Apple nows trades at 33 times earnings estimates for the next 12 months, above its five-year average of 27.5 times forward earnings. That multiple leaves little room for Apple to disappoint at WWDC.
Even if the company nails the presentation, don't expect Apple to get a near-term boost. Over the past decades, shares have declined slightly on the day of the WWDC keynote, according to Dow Jones Market Data. Three months later, they're up an average of nearly 14%.
Write to Angela Palumbo at angela.palumbo@dowjones.com
This content was created by Barron's, which is operated by Dow Jones & Co. Barron's is published independently from Dow Jones Newswires and The Wall Street Journal.
(END) Dow Jones Newswires
June 05, 2026 12:14 ET (16:14 GMT)
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